Sulfonium salts as pseudohalide electrophiles for cross-coupling having improved tractability, orthogonality, stability and environmental profile

Aim - Synthesise sulfonium salts for use as pseudo halides in cross-coupling reactions.
Objectives - 1) Optimise formation of sulfonium salts 2) Synthesise sulfonium salts of varying chemical nature 3) Use
sulphonium salts in cross coupling reactions such as Suzuki Cross Couplings, as pseudo halides 4)Perform
mechanistic studies for the cross-coupling
The potential applications of this research, are to enable new methods od synthesis in both the chemical industry and
academia, so called 'cross coupling' reactions have become a name stay of chemical synthesis over the last few
decades and their significance was acknowledged in the 2010 Nobel Prize. However, significant limitations remain in
the existing cross coupling methodology. The proposed sulphonium salts can be used in cross coupling reactions
where the corresponding halide (the 'traditional' starting material) is unstable, the monohalide is difficult to form or
challenging to purify etc. and so enables access to a wider range of molecules through cross coupling reactions.
The benefits of this research are that sulphonium salts are easier to handle, are usually more stable than the halides
they are replacing, and have a better environmental profile as pseudo halides for electrophiles in cross couplings
The project aligns with the EPSRC cross cutting capabilities of 'future manufacturing technologies' and 'advanced
materials' so is therefore relevant to the goals of the research council.
The secondary supervisor, Dr. Catherine Lyall has expertise in NMR spectroscopy and therefore will assist with
planned mechanistic studies using the Dynamic Reaction Monitoring Flow NMR facility